58845-84-4

Usage

Uses

Used in Pharmaceutical Industry:
(6R,6aβ,13R,13aα)-Dodecahydro-6,13-methano-10H-pyrido[1,2-a]pyrrolo[1,2-e][1,5]diazocin-10-one is used as a pharmaceutical compound for its potential therapeutic effects. (6R,6aβ,13R,13aα)-Dodecahydro-6,13-methano-10H-pyrido[1,2-a]pyrrolo[1,2-e][1,5]diazocin-10-one's unique structure may allow it to interact with specific biological targets, making it a candidate for the development of new drugs.
Used in Chemical Research:
In the field of chemical research, (6R,6aβ,13R,13aα)-Dodecahydro-6,13-methano-10H-pyrido[1,2-a]pyrrolo[1,2-e][1,5]diazocin-10-one can be used as a starting material or a reference compound for the synthesis of other complex organic molecules. Its unique structure may provide insights into the development of new synthetic pathways and methodologies.
Used in Material Science:
(6R,6aβ,13R,13aα)-Dodecahydro-6,13-methano-10H-pyrido[1,2-a]pyrrolo[1,2-e][1,5]diazocin-10-one may also find applications in material science, where its specific properties could be exploited to create new materials with unique characteristics. For example, it could be used in the development of advanced polymers, coatings, or other materials with specialized applications.

References

Santamaria, Khuong Huu Laine, Phytochem., 14,2501 (1975)

Upstream product

• 58845-83-3 (-)-camoensine 
• 155060-67-6 11α-(3,3-dimethoxypropyl)cytisine 
• 155060-68-7 11,12-dehydrocytisine 
• 485-35-8 cytisine 

Relevant academic research and scientific papers

(-)-Camoensidine N-oxide; a new alkaloid from Maackia tashiroi

A new alkaloid (3) was isolated from the stems of Maackia tashiroi (Leguminosae), together with (-)-camoensidine, tashiromine, ammodendrine and six known lupin (quinolizidine) alkaloids. The structure of 3 was characterized as the N15-oxide of (-)-camoensidine, possessing an indolizidine-quinolizidine ring system, by a combination of spectroscopic and chemical methods.

Diastereodivergent Synthesis of the Quinolizidine-Indolizidine Alkaloids of the Leontidine/Camoensine Family

Leontidine and camoensine, the main representatives of the small quinolizidine-indolizidine alkaloid subgroup, are characterized by an inner bispidine system to which a 2-pyridone and a pyrrolidine are fused on opposite sides. We efficiently synthesized both natural products from the commercially available and abundant alkaloid cytisine, which was converted into the key intermediate, N-Boc-11-oxocytisine, by iodine oxidation and protection. Grignard addition, Paal-Knorr type cyclization, and hydrogenation delivered endo-pyrrolidine fused leontidine, while the reversed reaction order, viz. reduction, Sakurai allylation, and ring closure, afforded exo-pyrrolidine annulated camoensine. Hydrogenation and deoxygenation of the pyridone moieties provided four further alkaloids, tetrahydroleontidine, camoensidine, 11-epileontidane and leontidane. In addition, the artificial alkaloid isoleontidine, carrying an endo-fused pyrrolidine on the same side as the pyridone, was prepared from C-13 oxidized cytisine.

Absolute stereochemistry of (-)-camoensine and (-)-camoensidine in Maackia species

It was demonstrated that the attack of Grignard reagents such as methyl-, allyl-, and 3,3-dimethoxypropyl magnesium bromides on 11,12-dehydrocytisine occurs on the α-face, to give the corresponding 11α-alkylcytisine. (-)-Camoensine and (-)-camoensidine were synthesized from (-)-cytisine via the Grignard reaction. The absolute stereochemistry of the above alkaloids was confirmed to be 7R, 9R, 11R and 6S, 7R, 9R, 11R, respectively.